The large quantity and low reactivity of methane has tantalized organic and organometallic chemists for years. The enormous quantity of methane that is produced at locations remote from natural gas pipelines has stimulated researchers throughout the petroleum industry to search for processes that can convert methane to more reactive and/or more easily transportable materials.
Various approaches to reaction of hydrocarbons have been studied over the years including thermal, chemical and photochemical. Examples of these are set forth in Janowicz and Bergman, J. Am. Chem. Soc. 105, 3929-3939 (1983). Most of these prior methods have consumed large amounts of energy in one form or another and suffered other disadvantages.
Recently it was reported that certain organoiridium complexes are capable of intermolecular oxidative addition to single C--H bonds in saturated hydrocarbons leading to hydridoalkyl iridium complexes which can be used to convert alkanes to alkyl halides. This is reported in, for example, Janowicz and Bergman, J.A.C.S. 104, 352 (1982). While these previously reported procedures have proven effective for a wide variety of alkanes, methane was not reactive under the conditions reported.